Published June 30, 2020
| Version v1
Journal article
Restricted
Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and noncanonical strigolactones in Lotus japonicus
Authors/Creators
- 1. ∗ & Department of Applied Life Sciences, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, Sakai, Osaka, 599-8531, Japan
Description
Mori, Narumi, Sado, Aika, Xie, Xiaonan, Yoneyama, Kaori, Asami, Kei, Seto, Yoshiya, Nomura, Takahito, Yamaguchi, Shinjiro, Yoneyama, Koichi, Akiyama, Kohki (2020): Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and noncanonical strigolactones in Lotus japonicus. Phytochemistry (112349) 174: 1-16, DOI: 10.1016/j.phytochem.2020.112349, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112349
Files
Restricted
The record is publicly accessible, but files are restricted to users with access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:FF80D61CD05A507AFF889C156513FFBA
References
- Abe, S., Sado, A., Tanaka, K., Kisugi, T., Asami, K., Ota, S., Kim, H. Il, Yoneyama, Kaori, Xie, X., Ohnishi, T., Seto, Y., Yamaguchi, S., Akiyama, K., Yoneyama, Koichi, Nomura, T., 2014. Carlactone is converted to carlactonoic acid by MAX1 in Arabidopsis and its methyl ester can directly interact with AtD14 in vitro. Proc. Natl. Acad. Sci. Unit. States Am. 111, 18084-18089. https://doi.org/10.1073/pnas. 1410801111.
- Akiyama, K., Matsuzaki, K., Hayashi, H., 2005. Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 435, 824-827. https://doi.org/10. 1038/nature03608.
- Akiyama, K., Ogasawara, S., Ito, S., Hayashi, H., 2010. Structural requirements of strigolactones for hyphal branching in AM fungi. Plant Cell Physiol. 51, 1104-1117. https://doi.org/10.1093/pcp/pcq058.
- Al-Babili, S., Bouwmeester, H.J., 2015. Strigolactones, a novel carotenoid-derived plant hormone. Annu. Rev. Plant Biol. 66, 161-186. https://doi.org/10.1146/annurevarplant-043014-114759.
- Alder, A., Jamil, M., Marzorati, M., Bruno, M., Vermathen, M., Bigler, P., Ghisla, S., Bouwmeester, H., Beyer, P., Al-Babili, S., 2012. The path from ss-carotene to carlactone, a strigolactone-like plant hormone. Science 335, 1348-1351. https://doi. org/10.1126/science.1218094.
- Baz, L., Mori, N., Mi, J., Jamil, M., Kountche, B.A., Guo, X., Balakrishna, A., Jia, K.P., Vermathen, M., Akiyama, K., Al-Babili, S., 2018. 3-Hydroxycarlactone, a novel product of the strigolactone biosynthesis core pathway. Mol. Plant 11, 1312-1314. https://doi.org/10.1016/j.molp.2018.06.008.
- Besserer, A., Puech-Pages, V., Kiefer, P., Gomez-Roldan, V., Jauneau, A., Roy, S., Portais, J.-C., Roux, C., Becard, G., Sejalon-Delmas, N., 2006. Strigolactones stimulate arbuscular mycorrhizal fungi by activating mitochondria. PLoS Biol. 4, e226. https:// doi.org/10.1371/journal.pbio.0040226.
- de Boer, T.H.J., Backer, H.J., 1954. A new method for the preparation of diazomethane. Recl. Trav. Chim. Pay-Bas 73https://doi.org/10.1002/recl.19540730308. 229-223.
- Boyer, F.-D., de Saint Germain, A., Pillot, J.-P., Pouvreau, J.-B., Chen, V.X., Ramos, S., Stevenin, A., Simier, P., Delavault, P., Beau, J.-M., Rameau, C., 2012. Structure-activity relationship studies of strigolactone-related molecules for branching inhibition in garden pea: molecule design for shoot branching. Plant Physiol. 159, 1524-1544. https://doi.org/10.1104/pp.112.195826.
- Brewer, P.B., Yoneyama, Kaori, Filardo, F., Meyers, E., Scaffidi, A., Frickey, T., Akiyama, K., Seto, Y., Dun, E.A., Cremer, J.E., Kerr, S.C., Waters, M.T., Flematti, G.R., Mason, M.G., Weiller, G., Yamaguchi, S., Nomura, T., Smith, S.M., Yoneyama, Koichi, Beveridge, C.A., 2016. LATERAL BRANCHING OXIDOREDUCTASE acts in the final stages of strigolactone biosynthesis in Arabidopsis. Proc. Natl. Acad. Sci. Unit. States Am. 113, 6301-6306. https://doi.org/10.1073/pnas.1601729113.
- Cardoso, C., Zhang, Y., Jamil, M., Hepworth, J., Charnikhova, T., Dimkpa, S.O.N., Meharg, C., Wright, M.H., Liu, J., Meng, X., Wang, Y., Li, J., McCouch, S.R., Leyser, O., Price, A.H., Bouwmeester, H.J., Ruyter-Spira, C., 2014. Natural variation of rice strigolactone biosynthesis is associated with the deletion of two MAX1 orthologs. Proc. Natl. Acad. Sci. Unit. States Am. 111, 2379-2384. https://doi.org/10.1073/ pnas.1317360111.
- Challis, R.J., Hepworth, J., Mouchel, C., Waites, R., Leyser, O., 2013. A role for MORE AXILLARY GROWTH1 (MAX1) in evolutionary diversity in strigolactone signaling upstream of MAX2. Plant Physiol. 161https://doi.org/10.1104/pp.112.211383. 1885-1902.
- Chojnacka, K., Santoro, S., Awartani, R., Richards, N.G.J., Himo, F., Aponick, A., 2011. Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis. Org. Biomol. Chem. 9, 5350-5353. https://doi.org/10.1039/c1ob05751k.
- Cook, C.E., Whichard, L.P., Turner, B., Wall, M.E., E G, 1966. Germination of witchweed (Striga lutea Lour.): Isolation and properties of a potent stimulant. Science 154, 1189-1190. https://doi.org/10.1126/science.154.3753.1189.
- Dieckmann, M.C., Dakas, P.Y., De Mesmaeker, A., 2018. Synthetic access to noncanonical strigolactones: syntheses of carlactonic acid and methyl carlactonoate. J. Org. Chem. 83, 125-135. https://doi.org/10.1021/acs.joc.7b02465.
- Flematti, G.R., Scaffidi, A., Waters, M.T., Smith, S.M., 2016. Stereospecificity in strigolactone biosynthesis and perception. Planta 243, 1361-1373. https://doi.org/10. 1007/s00425-016-2523-5.
- Fukai, E., Soyano, T., Umehara, Y., Nakayama, S., Hirakawa, H., Tabata, S., Sato, S., Hayashi, M., 2012. Establishment of a Lotus japonicus gene tagging population using the exon-targeting endogenous retrotransposon LORE1. Plant J. 69, 720-730. https://doi.org/10.1111/j.1365-313X.2011.04826.x.
- Gobena, D., Shimels, M., Rich, P.J., Ruyter-Spira, C., Bouwmeester, H., Kanuganti, S., Mengiste, T., Ejeta, G., 2017. Mutation in sorghum LOW GERMINATION STIMULANT 1 alters strigolactones and causes Striga resistance. Proc. Natl. Acad. Sci. Unit. States Am. 114, 4471-4476. https://doi.org/10.1073/pnas.1618965114.
- Gomez-Roldan, V., Fermas, S., Brewer, P.B., Puech-Pages, V., Dun, E.A., Pillot, J.P., Letisse, F., Matusova, R., Danoun, S., Portais, J.C., Bouwmeester, H., Becard, G., Beveridge, C.A., Rameau, C., Rochange, S.F., 2008. Strigolactone inhibition of shoot branching. Nature 455, 189-194. https://doi.org/10.1038/nature07271.
- Iseki, M., Shida, K., Kuwabara, K., Wakabayashi, T., Mizutani, M., Takikawa, H., Sugimoto, Y., 2018. Evidence for species-dependent biosynthetic pathways for converting carlactone to strigolactones in plants. J. Exp. Bot. 69, 2305-2318. https://doi. org/10.1093/jxb/erx428.
- Jia, K.-P., Baz, L., Al-Babili, S., 2018. From carotenoids to strigolactones. J. Exp. Bot. 69, 2189-2204. https://doi.org/10.1093/jxb/erx476.
- Kapulnik, Y., Koltai, H., 2014. Strigolactone involvement in root development, response to abiotic stress, and interactions with the biotic soil environment. Plant Physiol. 166, 560-569. https://doi.org/10.1104/pp.114.244939.
- Liu, J., Novero, M., Charnikhova, T., Ferrandino, A., Schubert, A., Ruyter-Spira, C., Bonfante, P., Lovisolo, C., Bouwmeester, H.J., Cardinale, F., 2013. CAROTENOID CLEAVAGE DIOXYGENASE 7 modulates plant growth, reproduction, senescence, and determinate nodulation in the model legume Lotus japonicus. J. Exp. Bot. 64, 1967-1981. https://doi.org/10.1093/jxb/ert056.
- Malolepszy, A., Mun, T., Sandal, N., Gupta, V., Dubin, M., Urbanski, D., Shah, N., Bachmann, A., Fukai, E., Hirakawa, H., Tabata, S., Nadzieja, M., Markmann, K., Su, J., Umehara, Y., Soyano, T., Miyahara, A., Sato, S., Hayashi, M., Stougaard, J., Andersen, S.U., 2016. The LORE1 insertion mutant resource. Plant J. 88, 306-317. https://doi.org/10.1111/tpj.13243.
- Matusova, R., Rani, K., Verstappen, F.W.A., Franssen, M.C.R., Beale, M.H., Bouwmeester, H.J., 2005. The strigolactone germination stimulants of the plant-parasitic Striga and Orobanche spp. are derived from the carotenoid pathway. Plant Physiol. 139, 920-934. https://doi.org/10.1104/pp.105.061382.
- Mori, N., Nishiuma, K., Sugiyama, T., Hayashi, H., Akiyama, K., 2016. Carlactone-type strigolactones and their synthetic analogues as inducers of hyphal branching in arbuscular mycorrhizal fungi. Phytochemistry 130, 90-98. https://doi.org/10.1016/j. phytochem.2016.05.012.
- Nelson, D.R., 2009. The cytochrome P450 homepage. Hum. Genom. 4, 59-65. https:// doi.org/10.1186/1479-7364-4-1-59.
- Nomura, S., Nakashima, H., Mizutani, M., Takikawa, H., Sugimoto, Y., 2013a. Structural requirements of strigolactones for germination induction and inhibition of Striga gesnerioides seeds. Plant Cell Rep. 32, 829-838. https://doi.org/10.1007/s00299- 013-1429-y.
- Nomura, T., Magome, H., Hanada, A., Takeda-Kamiya, N., Mander, L.N., Kamiya, Y., Yamaguchi, S., 2013b. Functional analysis of Arabidopsis CYP714A1 and CYP714A2 reveals that they are distinct gibberellin modification enzymes. Plant Cell Physiol. 54, 1837-1851. https://doi.org/10.1093/pcp/pct125.
- Pompon, D., Louerat, B., Bronine, A., Urban, P., 1996. Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol. 272, 51-64. https://doi.org/10.1016/S0076-6879(96)72008-6.
- Seto, Y., Sado, A., Asami, K., Hanada, A., Umehara, M., Akiyama, K., Yamaguchi, S., 2014. Carlactone is an endogenous biosynthetic precursor for strigolactones. Proc. Natl. Acad. Sci. Unit. States Am. 111, 1640-1645. https://doi.org/10.1073/pnas. 1314805111.
- Sun, H., Tao, J., Hou, M., Huang, S., Chen, S., Liang, Z., Xie, T., Wei, Y., Xie, X., Yoneyama, K., Xu, G., Zhang, Y., 2015. A strigolactone signal is required for adventitious root formation in rice. Anal. Bot. 115, 1155-1162. https://doi.org/10. 1093/aob/mcv052.
- Tokunaga, T., Hayashi, H., Akiyama, K., 2015. Medicaol, a strigolactone identified as a putative didehydro-orobanchol isomer, from Medicago truncatula. Phytochemistry 111, 91-97. https://doi.org/10.1016/j.phytochem.2014.12.024.
- Ueno, K., Nakashima, H., Mizutani, M., Takikawa, H., Sugimoto, Y., 2018. Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants. J. Pestic. Sci. 43, 198-206. https://doi.org/10.1584/jpestics.D18-021.
- Umehara, M., Cao, M., Akiyama, K., Akatsu, T., Seto, Y., Hanada, A., Li, W., Takeda-Kamiya, N., Morimoto, Y., Yamaguchi, S., 2015. Structural requirements of strigolactones for shoot branching inhibition in rice and Arabidopsis. Plant Cell Physiol. 56, 1059-1072. https://doi.org/10.1093/pcp/pcv028.
- Umehara, M., Hanada, A., Yoshida, S., Akiyama, K., Arite, T., Takeda-Kamiya, N., Magome, H., Kamiya, Y., Shirasu, K., Yoneyama, K., Kyozuka, J., Yamaguchi, S., 2008. Inhibition of shoot branching by new terpenoid plant hormones. Nature 455, 195-200. https://doi.org/10.1038/nature07272.
- Urbanski, D.F., Malolepszy, A., Stougaard, J., Andersen, S.U., 2012. Genome-wide LORE1 retrotransposon mutagenesis and high-throughput insertion detection in Lotus japonicus. Plant J. 69, 731-741. https://doi.org/10.1111/j.1365-313X.2011.04827.x.
- Wang, Y., Bouwmeester, H.J., 2018. Structural diversity in the strigolactones. J. Exp. Bot. 69, 2219-2230. https://doi.org/10.1093/jxb/ery091.
- Xie, X., Mori, N., Yoneyama, Kaori, Nomura, T., Uchida, K., Yoneyama, Koichi, Akiyama, K., 2019. Lotuslactone, a non-canonical strigolactone from Lotus japonicus. Phytochemistry 157, 200-205. https://doi.org/10.1016/J.PHYTOCHEM.2018.10. 034.
- Xie, X., Yoneyama, Kaori, Kisugi, T., Uchida, K., Ito, S., Akiyama, K., Hayashi, H., Yokota, T., Nomura, T., Yoneyama, Koichi, 2013. Confirming stereochemical structures of strigolactones produced by rice and tobacco. Mol. Plant 6, 153-163. https://doi.org/ 10.1093/MP/SSS139.
- Yoneyama, Kaori, Mori, N., Sato, T., Yoda, A., Xie, X., Okamoto, M., Iwanaga, M., Ohnishi, T., Nishiwaki, H., Asami, T., Yokota, T., Akiyama, K., Yoneyama, Koichi, Nomura, T., 2018a. Conversion of carlactone to carlactonoic acid is a conserved function of MAX1 homologs in strigolactone biosynthesis. New Phytol. 218, 1522-1533. https://doi.org/10.1111/nph.15055.
- Yoneyama, Koichi, Xie, X., Yoneyama, Kaori, Kisugi, T., Nomura, T., Nakatani, Y., Akiyama, K., McErlean, C.S.P., 2018b. Which are the major players, canonical or non-canonical strigolactones. J. Exp. Bot. 69, 2231-2239. https://doi.org/10.1093/jxb/ ery090.
- Zhang, Y., Cheng, X., Wang, Y., Diez-Simon, C., Flokova, K., Bimbo, A., Bouwmeester, H.J., Ruyter-Spira, C., 2018. The tomato MAX1 homolog, SlMAX1, is involved in the biosynthesis of tomato strigolactones from carlactone. New Phytol. 219, 297-309. https://doi.org/10.1111/nph.15131.
- Zhang, Y., van Dijk, A.D.J., Scaffidi, A., Flematti, G.R., Hofmann, M., Charnikhova, T., Verstappen, F., Hepworth, J., van der Krol, S., Leyser, O., Smith, S.M., Zwanenburg, B., Al-Babili, S., Ruyter-Spira, C., Bouwmeester, H.J., 2014. Rice cytochrome P450 MAX1 homologs catalyze distinct steps in strigolactone biosynthesis. Nat. Chem. Biol. 10, 1028-1033. https://doi.org/10.1038/nchembio.1660.
- Zwanenburg, B., Pospisil, T., 2013. Structure and activity of strigolactones: new plant hormones with a rich future. Mol. Plant 6, 38-62. https://doi.org/10.1093/MP/ SSS141.